My name is Jake and I’m a 58 year old stockbroker. I’ve been married and divorced twice and am now a confirmed bachelor. I keep myself in decent shape by regularly working out in a local gym and by running four days a week. At 5’10” and 175 pounds, I’m “average” sized, but I can hold my own in any situation I’ve come across.
My sex life is not bad…there are a lot of lonely women out there who are looking for a good, hard man and I have no problem finding a bed mate. Over the past few years of being single, I’ve been with more women than I can count, but each experience, whether good, bad or indifferent, has been a learning experience. I’ve learned, for example, that I am a “Dom” and like to control my sexual partner, and I prefer a “submissive” woman, sexually. I’m not into inflicting pain, but in some circumstances, it can be a powerful aphrodisiac. I find that my greatest turnon is having a woman under my control, and bringing her to a mindblowing orgasm, especially if she doesn’t completely expect it. I absolutely love to give a woman a “new” experience; one she has never had before, that leads to one of these super climaxes.
It is easy for a man to reach a climax, but many women seem to have a difficult time with it. Of course, everyone knows about clitoral stimulation, but many men are unaware of the “g” spot, just behind the clitoral area, but up inside the vaginal area. Not all women respond to this stimulation, but those that do tell me it is one of the deepest climaxes they have ever had. Most women love to have their mind stimulated, as well as their bodies, and once you have their attention, their sexual arousal can last for hours and they can’t wait to come back for more. Fortunately for me, a lot of guys are into self satisfaction first, and they leave the lady wanting more; and that is NOT a good thing.
I try to make it a rule not to mess around with anyone at work, and for that matter, to avoid being intimately involved with any customer, though some could easily be had. Most of my female clients are older and well past their prime, so they are not overly attractive, anyway. On occasion, however, I’ve seen an attractive client, either mine or one of the other brokers in the office, and I like to look, just like any other guy. I’ve also learned that the young “hardbodies” you run across in the single world often turn out to be airheads and ditzes, and I now avoid these like the plague. They may have gorgeous bodies, but they usually know nothing about satisfying a man.
I have a nice book of business, make a substantial living, drive a nice car, vacation to exotic places, live in an upscale condo in Scottsdale and have a terrific wine cellar. In other words, I’m considered a real “catch”, except for the fact that I am not available to be caught. Oh, and one other thing; I don’t usually mess with married women. They are available, mind you, but there are just too many complications. Which makes this story all the more unusual.
I inherited a couple who were clients of a broker that left the firm. Their account was not large; about $100,000 in total assets in the account. There were indications that they had more assets elsewhere, but the file didn’t indicate where. “Mike” and “Susan” also lived in Scottsdale, but were not close to me. The records indicated he was 40 and Susan was 38. He seemed to have a good income, and she was listed as a “housewife”, which indicated she didn’t work. They are not an “A” client, but I regularly call the lower ranked clients to touch base, and it occasionally uncovers other assets. One afternoon, I called their home, and Susan answered. I identified myself as their new broker, and asked if Mike was available. He wasn’t, and she told me he was traveling on business, but could she help? I explained this as a routine follow up, asked if they needed anything for their account; the usual chit chat, and then told her that if I could ever be of service, just give me a call, and I gave her my number and hung up.
A couple of days later, I was about to leave for the day and head out to a happy hour and look for some company, when my phone rang. It was Susan, and she said she just wanted to check on her account, etc. There wasn’t much to check on, since the account was pretty inactive, but she started asking me about myself, my background, my experience, my “family”, my marital status; none of which had anything to do with her account, but I thought she might be sizing me up for handling those other assets. Little did I know!
She asked about when I got off work, and I told her I was just about to leave when she called, and I was going out for “happy hour”, since I was single.
“I’ll bet all the ladies are after you when you walk in the door” she laughed when she said it.
“It’s not that simple” I laughed right back, “but I do alright for an older guy.”
“It’s no wonder. You have the sexiest voice on the phone I’ve ever heard” she said.
I was a little taken back by the comment. Yes, I’ve been told I have a pleasing, and even sexy, voice, which is helpful when you do a lot of business by telephone, but there seemed to be a bit more suggestiveness to her comment, than normal. All I could think of to say was “Thank you”.
“Where do you usually go for happy hour?” she asked.
I told her about a hotel bar in Scottsdale that often had flight attendants visit. “Oh, I know where that is, but I’ve never been there”.
I wasn’t sure, but she sounded like she was fishing for an invitation. “I’ll be there in about thirty minutes, so if you want to see what your new broker looks like, I’ll buy you a drink”. What in the hell am I THINKING?
“I may take you up on that” she said. “How will I recognize you?”
“I’ll be the older gentleman at the bar, wearing a navy blue suit, a powder blue tie, and a silly grin on my face” I joked.
“I may see you there. By the way, I like old fashioned martinis” and she hung up.
I had absolutely no reason to believe that she would really show up, and in fact, I was worried that she might. First of all, what would I do with her if she did, and secondly, she would blow my whole plan to get laid for the evening, and I hadn’t had a good piece of ass in over a week; I was more than ready.
I got to the bar about thirty minutes later, and ordered a Redbreast Irish whisky, on the rocks, and settled down to survey the landscape. It was still early and not much of a crowd, yet. Three obvious stews were huddled together at a corner table, but they were too young for my tastes. I’ve dated a couple of stewardesses, and they were nice to look at, but not that great in bed. I’ve found that attractive, older women are often the best; especially if I can show them new and exciting ways to climax. I had been there about fifteen minutes, when a voice said “Are you Jake?” I turned to look, and there stood a stunning redhead with green eyes and even without being obvious by looking, I could tell she had a gorgeous figure. She was wearing a green pantsuit with a cream silk tee underneath the jacket.
“Yes, that’s me” I grinned. “Are you, by any chance, Susan?”
“That’s me. Were you expecting someone else?” she smiled when she said it.
“No, of course not; I just didn’t expect you to really show up” I told her.
I called the bartender and ordered her an old fashioned martini (I remembered), and we moved to a booth near the wall. She was wearing a light fragrance that was very subtle, and as I got to look her over, I noticed her nails were French manicured and her skin was flawless. What was a gorgeous creature like this doing, meeting a virtual stranger in a bar?
As though reading my mind, she said “I don’t usually do this, but I’ve been cooped up in the house all week, and my husband will be gone for several more days, and I just need some adult companionship and conversation. I thought that since you are our broker, and you handle our money, I could trust you if we had a meeting.”
“Of course you can. I often meet with clients after hours, though I must say, never any as lovely as you” and I meant it.
She blushed and thanked me for the compliment. I told her it was a return favor for the “sexy voice” compliment she had paid to me. We chatted awhile and I learned she and her husband had been married for ten years, had no children, and she used to work as an executive secretary, but hadn’t worked for over a year. Her husband traveled as a salesman for a software company, and was gone most of the time. She let me know that she was lonely and just wanted someone to talk to, and that she really did love my voice. She also told me that now that she had met me, she found me to be extremely attractive; especially since I was an “older” man. She said it in a way that was complimentary, rather than being a putdown.
“Why do you think I’m attractive because I’m older?” I asked her.
“I don’t know. I just think you look like you might be…very experienced” she blushed when she said it. Suddenly, the sexual tension was so thick you could touch it, and my cock jumped to a semi alert stage. The lady was clearly sending a signal, but was I reading it correctly?
I looked her straight in the eye and said “As a matter of fact, I’m extremely experienced, and I’m an even better teacher, if someone is interested in learning new things.” I didn’t blink an eye, and my message was clear, so the ball was in her court.
“I’m always interested in learning new things; especially if the lessons are hard and perhaps even a little painful”. Oh my God, what have I stumbled onto here?
“I insist on controlling the curriculum, and my students seem to get full and complete satisfaction when we are through.” I smiled at her.
“Do you give private lessons at your home?” a blush had spread to her cheeks and up her neck, but I thought it was more from arousal than embarrassment. Just a hint of perspiration shown on her upper lip.
“As a matter of fact, I do. I was hoping to pick up a new student this evening, but I haven’t seen any who look worthwhile, until you joined me” I glanced down and noticed her jacket was open, and I could see one nipple clearly poking against the silk fabric of her blouse. “Would you like to go somewhere else to discuss this?”
“Yes, why don’t we.” She walked ahead of me toward the door and she had a nice, tight ass and her calves were nicely defined. Her hips swayed very subtly as she walked. She was about 5’5”, and I would guess her weight at around 125 pounds. She was slender but very nicely proportioned. I asked where her car was, and she pointed to a Cadillac nearby. “This is my Lexus. Why don’t you follow me, and I live just down the way about two miles” and I gave her directions of how we were going.
In my car, I was starting to get a raging hard on, and though I was breaking two of my own rules; the lady was married and she was a client, I had to follow through to see where this led. Ten minutes later, I pulled into my garage, and got out to direct Susan to the visitor parking spot. She slid out of the seat, and I directed her toward my condo. As she walked in front of me, I thought I detected a slightly damp spot on the back of her skirt. It was a match to the damp spot on the front of my slacks. I opened the door, and showed her in, offering her a drink. She asked for another martini, and I fixed it for her, but stayed with iced water for myself. I wanted to be fully functional. She took her jacket off and I hung it in the hall closet. The cream blouse was sleeveless, and both nipples were poking through the fabric. She was clearly aroused, and made no effort to hide it.
“So, how did I get so lucky that you want to become my ‘student’ all of a sudden? You are a gorgeous woman, and must be able to get your pick of men” I told her.
“The truth? My husband travels most of the year, and when he’s home, we have a reasonable sex life, but I know he gets ‘satisfaction’ when he is on the road. At home, it is just…boring. He simply does his duty, then is off on another trip. I make do with pleasuring myself and I have a few toys to play with that he doesn’t even know about. I haven’t been with another man, except in my fantasies, for several years. I was feeling very…aroused, when you called the other day, and I had just started to play with myself. Your voice…really is incredibly sexy, and I couldn’t help thinking about…what you might be like, when I played. It didn’t satisfy me completely, and I kept thinking about you until I got the nerve to call you again. Then, when I saw you, you were even better than I imagined. I know you must think me a slut, but I can’t help it; it’s the truth”.
“No, I don’t think you are a slut. Women have needs, too, I’ve discovered, and I take great pleasure in fulfilling those needs. But I have certain…methods, to bring out the very best. Are you sure this is what you want?”
She was looking me straight in the eye and without another word, began unfastening her slacks, and let them drop to the floor and stepped out of them. Her legs were shapely and well defined. She raised the top, and lifted it over her head. She was wearing white bikini briefs that were French cut, and the bra was a white lace number that had openings where her nipples protruded. I could see why she needed to wear such a bra because her nipples were almost an inch long and stood straight out from her very firm breasts. She reached behind her and undid the bra strap, letting it fall to the floor. Her breasts had almost no sag whatsoever. She slid the briefs down her legs and stepped out of them. As the old James Bond line once went, “collars and cuffs matched”; she had dark red pubic hair that had been shaved from the lips, but a triangle of it remained just above her slit. I couldn’t help but stare; her clit protruded from her slit, and was large and swollen. It almost looked like a miniature penis, and was the largest clit I had ever seen on a woman.
I led her to the bedroom, and told her to sit on the edge, and then lay back while I undressed. She followed my instructions, while I put my clothes away. I took my time, because the arousal was already there, and the anticipation would just make it more intense. When I was completely undressed, I turned, and saw her looking at my fully erect cock. I am circumcised, and my cock is very thick and around seven and a half inches…normal by any standard.
“You have incredible nipples…and your clit is very…prominent” I said to her.
“I know...they’ve always been large, I don’t know why. I wasn’t aware of them being unusual until I saw some other girls in my PE class. I’ve seen pictures of naked women in men’s magazines, but none seem to have this…prominence” she said. “I don’t worry about them, but they are easily stimulated just by my clothes, and I can’t help…getting turned on, even when I don’t mean to.”
“Well, let’s just see what we can do about that” I grinned at her. I climbed on the bed and crawled to behind her head, with my knees on either side of her head. My cock dangled over her face, and a drop of pre-cum dripped on her cheek. I reached out and took both of her nipples between my thumbs and forefingers and began to roll them, squeezing and releasing, then repeating the process. After a couple of minutes, I shifted to stroking around the outside of her breasts, now avoiding the nipples because I knew they were sensitive, and knew she wanted me to touch them. I could see her clit clearly, and it was throbbing, literally like a little cock, pumping up and down in the air from her slit. She was breathing heavily, and there was perspiration showing under her breasts. She moaned every time my fingers got close to those nipples, and she softly said “please” more than once. I ignored that, and kept teasing. Finally, I reached out and pinched her right nipple and twisted it; her body jerked, and her hips convulsed up and I could see the inside of her thighs were soaking wet. She had had a minor orgasm from the breast manipulation, and was gasping as I knelt over her. My semen had flowed freely, and her face was wet with it, but she didn’t even notice. She was “gone” into the moment.
I moved off the bed, and walked to the foot and knelt between her thighs. I lifted her feet up and put one on each shoulder and then leaned forward, staring at that magnificent, huge clitoris. I snaked my tongue out, and with the lightest touch I could manage, I just touched the tip of her clit with the tip of my tongue. Her hips jerked up and she tried to push it against my face, but I pulled back away, and blew a soft breeze right at her clit. She was moaning and talking, but the words were unintelligible; it was clear she wanted more…much more. I licked the inside of her thighs; both sides, but stayed away from her slit until finally, I ran my tongue from the bottom to the top, flicking her clit at the end. Her whole body convulsed as she released another climax, but again, it was minor.
I decided to check out her g-spot, and slipped my finger in her totally flooded channel, and curled the tip up to the soft spot just behind the pubic bone. Her body jerked as though hit with a jolt of electricity, and this time, I kept up the gentle massage as wave after wave of orgasmic spasm washed over her. Susan was almost delirious after this more complete climax. I was getting a bit tired, having worked on her for so long, and I needed relief, myself. My balls were throbbing, and I had been in a state of arousal for almost two hours. Talk about blue balls! I stood between her legs, and pulled them over my shoulders, raised her ass off the bed, then slid my cock into her opening. Even though she wasn’t a virgin, her pussy was tight and my cock is very thick. She started mumbling again, and I could only make out “oh, yes…oh, yes” as I began to stroke into her. With her ass up in the air, and from this position, I could penetrate her completely and I could feel the head of my cock against her cervix. I kept pounding as hard and as deep as I could for about five minutes, but then I could no longer hold back, and my balls contracted and my cock almost exploded with one of the largest loads I have ever shot, straight into this gorgeous redhead. Even as I was cumming, I felt the walls of Susan’s pussy contracting around my cock as she had yet another orgasm. Her contractions were so strong, that they eventually squeezed my softening cock out of her before I could even withdraw. I can honestly say this was one of the most fantastic fucks I have ever had.
I collapsed on the bed beside her and we both lay there panting and gasping for breath. I felt drained. I must have dozed off, because the next thing I remember was waking to find Susan kneeling on the floor between my legs, gently washing my cock and balls with a warm wash cloth. She smiled at me when I opened my eyes, and said “That was the most fantastic sex I’ve ever had. Is there more where that came from?”
I grinned at her and replied “Of course, but you need to understand that while ‘older’ men are more experienced, we don’t have quite as much stamina as the younger studs”.
“If that is just a sample, I’ll take the experience over stamina any day!”
This was just the first of many “services” I performed for Susan for the next couple of years. Let me know if you would like to hear about any of my “other” services.